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cleighwrites · 5 years ago

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Branching Out pt7

SPN Fanfic

Characters - Dean, Stacey and Vinny and Billy (OMCs) mentioned.

Summary - Dean leaves Stacey's and can't stop thinking about what he'd just done

Word Count - 1,725

A/N - Since this is a prequel to my Wincest Big Bang there will be some wincestual feelings. Dean's working at a garage and Sam is in his junior year of high school. Beta/editing by @mrswhozeewhatsis and @deanwinchesterswitch

Warnings - SMUT, anal (first time: fingering and sex), self examination

Part 6 - Series Master List

Dean stared at his steering wheel for what seemed like hours when he got into his car. He held his hands up in front of his face and studied them. Remembering what it had felt like to wrap them around another man’s cock, how tight and hot it had felt being knuckles deep in his ass. More importantly, Dean remembered how none of it felt wrong or dirty; it felt different, but in a good way.

Dean turned the key and felt the familiar rumble of Baby’s engine turning over; at the same time, he felt his dick twitch at the memory of Stacey wrapped tight around him, how his muscles had gripped him even tighter when he came. It wasn’t the same as being with a woman, for obvious reasons, but it was similar enough that Dean had gained his confidence fairly quickly once things had picked up.

The entire drive back through town, Dean couldn’t stop thinking about everything that had happened. He replayed it over and over again, trying to figure out how he really felt about it.

Stacey tugged on Dean’s bottom lip as he broke the kiss. He searched Dean’s face before sliding his fingers over the bulge growing behind the borrowed slacks. Dean groaned at the firm touch of the man’s long fingers and arched his back to get more friction. Stacey smirked at him, gave his cockhead a gentle squeeze, then backed away.

A whine slipped from the back of Dean’s throat, but any further protest was quelled by Stacey’s outstretched hand. Dean let Stacey lead him out of the closet and back into his massive bedroom. They stopped at the foot of the bed where Stacey took his time undressing Dean. He paid special attention to Dean’s nipples and hip bones, Stacey seemed to also enjoy feeling up Dean’s ass.

It wasn’t like Dean had never had his ass played with before, but there was something about the strength and size of Stacey’s hands that had Dean almost begging for more. More of what, Dean couldn’t really say; just more. Stacey gave Dean the choice, top or bottom; Dean still wasn’t sure exactly how things worked, but he knew he was good at fucking women, and how different could it really be to fuck a man? So, he chose top.

After removing his own clothes, Stacey sat on the corner of the bed and pulled Dean down beside him. They kissed again until Dean’s body relaxed, then they laid down, and Dean let his hands roam. Stacey was hard between them and Dean felt the wet tip brush against his fingers as he moved his hand to grab Stacey’s hip. Stacey hummed and bucked his hips, rubbing his length into Dean’s hand.

Dean only thought about what he should do for a split second before letting his instincts take over. He wrapped his fingers around the other man’s cock and began to stroke him. He alternated pressure and twisted his wrist until he found the exact way to stroke him that had him moaning and gasping. Stacey returned the favor, and Dean could swear that he had never been jerked off as good by anyone else before, not even himself.

It wasn’t too much longer before Stacey lubed up three of Dean’s fingers and guided them to his ass. He was laying flat on his back and had his legs spread, knees tucked up toward his shoulders. Dean had never seen a man spread out for him like this. He could see everything. Stacey’s dick, heavy and leaking on his belly, his bare balls hanging down leading to his clean-shaven asshole.

The pink, fleshy pucker was flexing, waiting for Dean’s touch. He knew the mechanics well enough, just like getting a girl ready for him, he’d have to work on the muscles, get them loose and pliant so Dean could get his cock in there. Of course, Dean also knew about a man’s prostate; not that he’d ever gone searching for one before, but he knew that would feel good for Stacey.

“Just start with one finger,” Stacey instructed. “You’ll feel how tight it is, when I loosen up, add another, then scissor your fingers.” Stacey wiggled his fingers in demonstration. “Don’t worry about doing anything else.”

Dean licked his lips nervously as he looked away from Stacey’s face and back down to where his fingers were hovering over his entrance. Stacey hissed in a breath when Dean finally applied pressure to his hole, the tip of his middle finger barely pressing in. He found his rhythm quickly, and before too long was fucking him with three fingers down to the knuckle.

One particular flick of his wrist and Dean felt a little bundle brush against one of his fingers, Stacey’s hips bucked and he moaned, fisting the sheets. Dean found the bundle again and rubbed against it deliberately, making Stacey arch off the bed and start to fuck himself on Dean’s hand. He couldn’t help the self-confident smirk that had spread across his face.

“Mmm, Dean!” Stacey yelled. Dean worked his fingers harder. “Oh, god! Dean, fuck me!”

Dean’s dick twitched and Stacey threw a condom at him when he eased up his ministrations. Stacey stroked himself while Dean slid his condom on and lubed up his cock. He had a moment's hesitation when he lined himself up, he looked to Stacey, who smiled and nodded at him to continue. Dean pushed but was met with such resistance he was sure he hadn’t prepped him enough.

Stacey put his hand over Dean’s on his thigh and squeezed it. “It’s going to feel very tight at first. Keep going, once you get the head through, everything else will work out. It’ll fit, I promise.”

Dean had never had a pep talk during sex before, but it was kind of hot. It was almost painful on his tender head to shove against the tight ring of muscle so hard, but Stacey was right, once he got his head all the way in, and he felt that tight heat open up around him, it was like nothing he had ever felt before. He slid slowly all the way in, for the first time. Dean wasn’t one to brag, but he was rather large and no woman he had ever been with had been able to take all of him.

Having those hot, tight muscles flutter around his entire length was almost enough to make Dean come right away. He held his breath and focused on his hands on Stacey’s legs. Once he was sure he could handle it, he pulled out a little, the stretch and pull of skin around him was mind-blowing. Dean settled for short thrusts until he couldn’t stand it anymore and began to fuck into Stacey like his very life depended on it. Long, hard, deep thrusts that had his balls slapping against Stacey’s ass.

Stacey was trying to meet Dean’s thrusts but gave up and just laid there while Dean fucked into him. Sometimes he would grab at Dean’s hands or his ass, sometimes his hands would run through and pull his own hair; Dean liked it best when his fists were white-knuckled into the comforter. His husky breaths and deep moans of pleasure drove Dean wild with want.

Women didn’t sound like that when he fucked them; Dean wanted to hear this man come apart beneath him. He knew when he found Stacey’s prostate and made sure to thrust at that same angle as often as possible. When Stacey started to squeeze even tighter around him, Dean saw his balls drawing up, so he wrapped his hand around Stacey’s cock and held it tight. On a deep thrust, Dean jerked him once, flicking his wrist just under his head, and Stacey came with a strained grunt.

The velvety constriction pulsing around him as Stacey came had Dean thrusting erratically until he finally shoved in deep and emptied his own release into the condom. Sweat was running down his face and his knees were shaking as he held the condom and pulled out. Stacey’s legs fell flat onto the mattress and his arms were covering his face. Stacey laughed.

Dean’s heart sank for a moment until Stacey moved his arms and looked him in the eye. “There’s no way… you’ve never… fucked before, Dean. No one’s… that good… their first time.” He was breathing heavily and laughed again when he finished talking.

“Well, I don’t know what to tell you.” Dean sat somewhat awkwardly on the end of the bed as he pulled the condom off. “Um, where-”

“There’s a trash can right here.” Stacey’s arm flung haphazardly toward the edge of the bed pointing vaguely beside the nightstand.

Dean got up, walked over, and threw the condom into the decorative metal bin. As he turned to face the bed, Stacey gripped his hip and pulled him down to lay beside him. Dean had only ever snuggled like this with Sam when they had shared a bed when they were younger, and on more than one occasion as they got older, when there was no heat in the house. But it hadn’t been like this.

Dean had a fleeting thought about how nice it would have been if it had been. He shook the thought from his head and let Stacey burrow into his shoulder. Neither Lisa nor Anna had wanted anything to do with him after they had gotten off, so Dean wasn’t entirely sure what to do. He figured that Stacey was the one paying for it, so he’d let him drive.

They laid there until their breathing was steady, and just as Dean’s arm was starting to go numb Stacey stirred and sat up.

Dean shook his head and realized that he was parked down the alleyway where he’d met Billy and Vinny earlier that night. He took the wad of cash that Stacey had slid in his back pocket as he kissed him goodbye and shoved it into the glove box. Dean had given him a look and Stacey had just winked and told Dean he’d earned it, then he handed him the envelope for Vinny. He grabbed the other two envelopes of cash, locked the doors, and knocked on the door where he had met Vinny previously that night.

Part 8

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